Rosie O'Donnell says end of her friendship with Ellen DeGeneres was 'one of the most painful things'

DUBLIN, IRELAND: Rosie O’Donnell has candidly revisited the collapse of her decades-long friendship with Ellen DeGeneres, describing it as one of the most devastating experiences of her career.

Speaking on the September 7 episode of Mamamia’s 'No Filter' podcast, O’Donnell, 63, recalled the moment everything changed.

Rosie O’Donnell opens up about painful rift with Ellen DeGeneres

The falling-out traces back to a 2004 appearance on 'Larry King Live', where DeGeneres, now 67, denied being friends with O’Donnell. For O’Donnell, the dismissal cut deep, particularly because she had been one of DeGeneres’ most public allies during the star’s coming-out in 1997.

“That was like one of the most painful things that ever happened to me in show business in my life,” O'Donnell said, adding, “I have photos of her holding my newborn babies. I knew her for 30 years. She was, all of a sudden, in the position I was in and instead of deciding to stand next to me and hold my hand, which is what I did to her, she did the opposite.”

The actress and comedian said she had known DeGeneres for three decades and even had photos of her cradling her newborn children. “I couldn’t believe it,” she admitted.

Revisiting the rift over the years

Rosie O’Donnell emphasized that she doesn’t bring up the incident for “pleasure,” as she believes DeGeneres might assume, but rather because their careers have long mirrored one another.

“I would have apologised but I think in her mind, she thinks I keep rehashing it for pleasure. I don't rehash it for pleasure. I rehash it because our careers have taken sort of parallel, interwoven paths,” O’Donnell added.

The story has resurfaced multiple times, including in 2022 when O’Donnell discussed it on 'Watch What Happens Live with Andy Cohen'. That interview reportedly caught DeGeneres’ attention, prompting her to reach out in 2023 with an apology.

“She texted me a few weeks ago, checking in and seeing how I’m doing,” O’Donnell told The Hollywood Reporter at the time. “She wrote, ‘I’m really sorry, and I don’t remember that.’”

For O’Donnell, however, the incident was unforgettable. She remembered it so vividly that she even printed T-shirts for her staff emblazoned with the phrase “I don’t know Rosie. We’re not friends.”

“It just felt like, I don’t trust this person to be in my world,” she explained.

Both women’s personal and professional lives have continued to intersect in unexpected ways. O’Donnell relocated to Ireland earlier this year, while DeGeneres moved to the UK with her wife, Portia de Rossi, in 2023.

Their names were linked again over the summer when Donald Trump lashed out at O’Donnell, threatening to revoke her US citizenship and labeling her a “threat to humanity.” O’Donnell had openly criticized his administration and said her relocation was partly a way to escape the political climate.

DeGeneres, despite their complicated history, publicly supported O’Donnell in July. Sharing both Trump’s post and O’Donnell’s response on Instagram, she added, “Good for you.”